Tryptoline

Tryptoline
IUPAC name 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole
Other names Noreleagnine Tetrahydronorharman 2,3,4,9-Tetrahydro-1H-β-carboline
Identifiers
CAS number	16502-01-5
PubChem	107838
ChemSpider	96979 Y
ChEMBL	CHEMBL269236 Y
Jmol-3D images	Image 1
SMILES c3c1c(nc2c1CCNC2)ccc3
InChI InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Y Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N Y InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Key: CFTOTSJVQRFXOF-UHFFFAOYAW
Properties
Molecular formula	C11H12N2
Molar mass	172.226 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of beta-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.

Pharmacology

Many tryptolines are competitive selective inhibitors of the enzyme monoamine oxidase type A (MAO-A). 5-Hydroxytryptoline and 5-methoxytryptoline are the most active monoamine oxidase inhibitors (MAOIs) with IC₅₀s of 0.5 μM and 1.5 μM respectively, using 5-hydroxytryptamine (serotonin) as substrate.

Tryptolines are also potent reuptake inhibitors of serotonin and epinephrine, with a significantly greater selectivity for serotonin. Comparison of the inhibition kinetics of tetrahydro-β-carbolines for serotonin and epinephrine reuptake to that of the platelet aggregation response to these amines has shown that 5-hydroxymethtryptoline, methtryptoline, and tryptoline are poor inhibitors of reuptake. In all respects 5-hydroxytryptoline and 5-methoxytryptoline showed greater pharmacological activity than the tryptoline and methtryptoline.

Although the in vivo formation of tryptolines has been a matter of controversy, they have profound pharmacological activity.

See also

• Norharmane
• harmane
• beta-Carboline
• Harmala alkaloid

References

• H. Rommelspacher, H. Kauffmann, C. Heyck Cohnitz and H. Coper (1977). "Pharmacological properties of tetrahydronorharmane (Tryptoline)". Journal Naunyn-Schmiedeberg's Archives of Pharmacology 298 (2): 83–91. doi:10.1007/BF00508615. http://www.springerlink.com/content/g264075045877742/.